Questions tagged [inductive-effect]
Use for questions regarding the so called inductive effect of substituents on properties of compounds.
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Reactivity of Alkenes with HBr
I am new in the Organic Chemistry (World of Reactions). I had got one question in my test. But, when I had seen it, I got no proper logic to tick the correct answer, and then when I saw solution, then ...
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Inductive Effect of -CH3 group
3° carbocations are the most stable because of the +I effect of -CH3 group. This group gives a slight negative charge to the central carbon atom, which makes it less positively charged and thus, more ...
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Does inductive effect operate through pi bonds?
I have been told that the inductive effect is only present in sigma bonds by my teacher, and the book I've referenced also says the same thing.
However, I can't think of why this is. Answers to this ...
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Why does chlorine show a mesomeric effect in haloarenes and an inductive effect in haloalkanes?
Chlorine shows the +R effect in haloarenes and the -I effect in haloalkanes. Does chlorine do the same for all cyclic compounds or only for aromatic rings? Is this just another experimentally seen ...
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Difference between nucleophilicity of phenoxide ion and acetate anion in protic/aprotic solvent
As far as I could think, the phenoxide ion is comparatively larger as compared to acetate ion, so it should undergo less solvation in presence of a protic solvent and thus its nucleophilicty should be ...
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Ortho effect and the relative acidity in aromatic acids [duplicate]
What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid?
I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
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157 views
How come the methyl group (-CH3) is electron donating?
If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
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Why is the carbanion stability order the way it is? (3*<2*<1*)
According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help)
With my very ...
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Hydrogen as a reference in inductive effect
What does it mean when we say that I-effect of hydrogen is taken as zero ?
I think that it means that partial displacement of sigma bond electrons between two atoms of different electronegativity is ...
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1answer
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Why don't we consider the attached hydrogens in inductive effect?
Consider the molecule 1-chloroethane
Let carbon attached to $\ce{Cl}$ be $\ce{C1}$ and other one be $\ce{C2}$. While learning inductive effect I was told that $\ce{Cl}$ due to high electronegativity ...
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136 views
Why is ethanol more acidic than acetone?
The acidity of a compound is determined by the stability of its conjugate base and the major structure of enolate has a negative charge on the Oxygen atom. Moreover, the negative charge on the O-atom ...
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Effect of distance on the mesomeric effect
I have always thought that mesomeric effect is somewhat dependent on distance.
But I recently came across a question where I was asked to predict the order of stability of o-methoxyphenyl carbocation ...
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258 views
Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?
If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows:
Even after deprotonation, it has intramolecular hydrogen bonding as follows:
My question:
p-...
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1answer
160 views
Stability of meta ethyl and meta methyl benzene carbocations respectively
It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
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1answer
46 views
Carbocation formation and stability from bromo compounds
When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
This is my ...
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Comparing nucleophilic strengths of tetrahydropyran and (2R,6R)-2,6 dimethyltetrahydropyran
Compare the nucleophilic strengths of the following two compounds:
According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I ...
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How do steric effects affect inductive effect in compounds with tetravalent nitrogen?
I want to compare the electron density on methyl group between tri‐tert‐butyl(methyl)azanium (1) and triisopropyl(methyl)azanium (2), i.e. essentially the inductive effects of $\ce{-\overset{+}{N}R3}$ ...
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Evaluating inductive effects in cyclic compounds
I was required to find the products on heating the hydroxide of;
Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
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238 views
Acidic nature comparison; benzoic acid and phenylacetic acid
The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively.
In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
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157 views
What does acidity of para-alkyl substituted phenols depend on?
Problem
Arrange the following organic compounds in decreasing order of acidity.
Answer
Question
According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
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1answer
131 views
Stabilization of multiple bonds through inductive effects
In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
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Why does the carboxylate ion show positive inductive effect?
While solving some problems on general organic chemistry, I came across this question that asked for the nature of inductive effects of $\ce{-CH_3}, \ce{-CO_2^-}, \ce{-Br}, \ce{-NH_3^+}$.
And in the ...
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Confusion in comparing the contribution of resonating structures to resonance hybrid [closed]
So I was comparing the $+M$ effect of $\ce{-CH^-_2}$, $\ce{-NH^-}$ and $\ce{-O^-}$. Answer was given as:
$$ \ce{-CH^-2 > -NH^- > -O^-}$$
So, I attach them with ethene and made their respective ...
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1answer
113 views
Relative acidity of acetic acid derivatives with strongly withdrawing substituents
What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following:
$\ce{O2N-CH2-CO2H},$
$\ce{Me3\overset{+}{N}-CH2-CO2H},$
$\ce{NC-CH2-CO2H},$
$\ce{HO-CH2-CO2H}?$
Since only the groups ...
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Combined Effect of Steric Inhibition of Resonance and Inductive Effect
While qualitatively comparing the acidic nature of o-methyl benzoic acid and benzoic acid, we consider the steric effect due to which the $\ce{-COOH}$ group loses its planarity and the +M effect of $\...
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1answer
123 views
How to explain regioselectivity in nucleophilic aromatic substitution
I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide:
I have predicted that the para-substituted product is formed as ...
2
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1answer
81 views
Order of −I effect among ethenyl and 1-propenyl groups
We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power?
The $\...
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1answer
267 views
Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?
I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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1answer
285 views
Estimation of dipole moments in aromatic compounds
If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both?
E.g. we have to compare dipole moment in pyrrole and furan then in ...
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Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
Beginning with a reference to a well known question.
Order by reactivity towards SN1 reaction.
According to some facts about SN1 reactions, rate depends on:
Stability of carbocations
Better leaving ...
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143 views
Inductive effect of acetyl group
Question:
Since the acetyl group provides $-M$, methyl $+I$ and chlorine $-I$, it is obvious that the correct order is as given in option $(a)$
However while solving such questions I would compare ...
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236 views
Does the electron displacement effect act only on sigma electrons?
Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be.
I reasoned it can not affect the pi ...
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1answer
433 views
Carbanion Stability order [duplicate]
Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...
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1answer
300 views
The most acidic hydrogen among ethane, ethene, ethyne and allene
Among
$$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$
I need to find out the one having highest acidic hydrogen.
As per my observations, there are two equivalent resonating ...
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1answer
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Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?
Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
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2answers
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Does Cl- Have more -I effect or +M effect ( Resonance effect)?
In this question my answer was (A) because i though $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$ . But the correct answer is (D) and my teacher's reason is that chlorine has more ...
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1answer
102 views
Inductive effect of -NHMe
Why does $\ce{-NHMe}$ show -I effect. I think it should be opposite. I know that $\ce{-Me}$ groups are electron donating in nature. So the nitrogen atom will have a small $\delta^-$ charge. So then ...
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Methyl group and acidic nature [duplicate]
After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
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1answer
723 views
Why is formic acid stronger than acetic acid [duplicate]
Even when acetate ion is stabilized due to resonance why is it a weaker acid than formic acid. It is true that acetic acid has +I effect due to methyl group present on it but resonance is a stronger ...
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Problem in defining the Inductive effect
Inductive effect is introduced in many textbooks by giving an example of an alkyl halide $R-X$.
The bond C1-X is polar due to electronegativity difference, therefore X gains partial negative charge ∆(-...
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1answer
405 views
Stability of carbocation directly attached to a halogen atom [duplicate]
I have two compounds..
How is the first one more stable?
As I have been taught that -I effect of Chlorine dominates its +R effect but to explain this case, My teacher is saying that because of the ...
0
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1answer
99 views
Para effects on substituents in aromatic compounds
I wanted to know how to compare the following compounds on basis of acidic strength.
I have to find the acidic strength of following compounds with $\mathrm{X}=\ce{CH3, \ OCH3,}$ and $\ce{NO2}$.
For ...
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0answers
561 views
Comparison of basicity of Aniline, p-Anisidine, and o-Anisidine [duplicate]
I have a question where I am required to compare the basicity of Aniline, o-Anisidine, and p-Anisidine.
Now here's what I do know:-
In ortho substituted aniline, an ortho effect acts which reduces ...
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Comparison between groups with -I effects
So I have a few questions in my book that require me to compare between two different groups on the basis of their -I effects. I have a few questions on this that have been bugging me for quite a ...
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1answer
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Effect of phenyl and vinyl substituents on Acidity of carboxylic
Recently I came across this statement in my textbook:
Direct attachment of groups such as phenyl or vinyl to the carboxylic
acid, increases the acidity of corresponding carboxylic acid contrary
...
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3answers
216 views
Odd looking carbocation stability order [duplicate]
I am studying introductory organic chemistry, suddenly this one started looking odd,
The carbocation stability for three compounds as given by my book is shown below,
Let me call those as ...
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1answer
249 views
Change in inductive effect of a susbstituent when -R group replaces -H atom
There are several examples where the negative inductive effect of a substituent gets increased when a hydrogen atom on that substituent is replaced by an alkyl group.
Some particular examples:
$$\ce{...
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Why O and N promote SN1 but C=O inhibit SN1 although both are electron-withdrawing?
Source:
Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry 2th Edition, 339.
The general idea I got so far, is that, carbocation will be more stable if the + charge at central C is ...
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0answers
143 views
How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?
I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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1answer
204 views
What is the stability order of the carbocation and carboanion?
So I came up with examples as below:
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2
Now I am confused about the +I and -I effect in these structures since to my knowledge it can only be applied when there is a substituent (I might be wrong)...
